SCIENCE. 



323 



another element than the distortion or displacement to 

 which Dr. Chapman very properly refers, namely, the 

 position in which the brain is held or placed. In Dr. 

 Chapman's figures, the organ rests upon the medulla, 

 and upon the ventral aspects of the frontal and temporal 

 lobes ; were it brought into something approximate to 

 its natural position, or to the position of the human 

 brain, the occipital lobes would surely project beyond 

 the cerebellum to an appreciable extent. It would be 

 well if the next Orang's head should be sawn into sec- 

 tions parallel with the mesial plane, and the brain figured 

 in situ. 



It is gratifying to find Dr. Chapman, like Humphrey 

 and Barnard, insisting that the " scansorius " muscle of 

 Traill is really the entoglutaeus. But Dr. Chapman 

 does not seem to have observed the curious little muscle 

 passing over the capsule of the acetabulum which Prof. 

 Barnard has called " ilio-femoralis subrectus," and 

 which, in the opossum, Coues seems to have mistaken 

 for the unlucky " scansorius." 



A novel and significant suggestion is that, " morpho- 

 logically speaking, the laryngeal pouch of the anthro- 

 poids would be homologous with and replace the two 

 layers of the cervical fascia in man." 



This otherwise very commendable paper is marred by 

 some important misspellings, as of ilium which is made 

 ileum twice on page 4, and by an occasional obscurity of 

 style which sometimes renders the author's meaning 

 doubtful. B. G. W. 



theory as to include naphthaline, which he considered as 

 having been derived from two benzol rings possessing 

 two carbon atoms in common. 



ON THE CONSTITUTION OF THE NAPHTHA- 

 LINES AND THEIR DERIVATIVES. 



1 Translated from the German.! 

 By M. Benjamin, Ph. B., and T. Tonnele, Ph. B.- 



Among the many aromatic hydrocarbons, naphthaline 

 is one of the most interesting. The causes and laws of 

 isomerism may be studied trom the numerous isomeric 

 compounds on one hand, while on the other, much in- 

 formation is derived from the consideration that many of 

 these have acquired a great importance in the technical 

 arts. In consequence of this, a great number of memoirs 

 exist on this subject, and they are scattered abroad 

 among the numerous scientific journals. It is, therefore, 

 no simple matter for one to obtain a clear survey cf the 

 naphthaline question. We hope that the following 

 pages, comprising material originally collected for our 

 own information, will be welcomed by such of our pro- 

 fessional colleagues as may have occasion to study this 

 subject, for we feel assured that by consulting ihis article 

 much of their time and labor will be economized. 



CONSTITUTION" OF NAPHTHALINE. 



Naphthaline was discovered in 1826, by Garden, and 

 subsequently widely studied by many investigators ; yet 

 its constitution remained undetermined for more than 

 forty years. In the year 1866, Kekule 1 published his in- 

 genious and fertile theory of the aromatic compounds, 

 considering them as derivatives from a singh hydrocar- 

 bon, benzol. Soon after Erlenmeyer- so extended this 



* Note. — The following memoir, written by MM. F. Reverdin and t. 

 Notting, was published in Geneva early this year. In addition to the 

 text herewith given, the original pamphlet was supplemented with several 

 valuable tables. These showed the derivation and behavior with reagents 

 of the various substitution products, it is with regret that we are obliged 

 to omit them. The space which they would occupy, tog- ther with the 

 fact that they are not of general interest, doe> not seem to warrant their 

 insertion. The entire article is undoubtedly the best resume of the differ- 

 ent theories concerning the formation of the naphthalines in existence. 

 1 Translators.) 



1 Annalen der Chemie und Pharmacie, vol. CXXXVU. p. i2 y 11866). 

 - .Ann. Chem. Pharm., CXXXVU, 346 (i866>. 



* Ann. Chem. Pharm., CXLIX, 1 1:869). 



* Ann. Chem. Pharm.. CXI. II, 2:1 '1867). Compter Rendus. 

 LXIII, 788 and 834. 



/ ■■// 



c 



" / 



c c 



Graebe 3 was the first to demonstrate the correctness ot 

 this theory, in the course of his remarkable researches on 

 the chinones of benzol and naphthaline. Since then this 

 theory has been sustained by a large number of facts, 

 while no satisfactory objections have been brought for- 

 ward against it. 



Other formulae have been proposed by Berthelof, and 

 later by Ballo 5 , and also by Wredeh 8 , but none of 

 these have received the approval of chemists. 



The following are the principal facts which support 

 the formula given by Erlenmeyer and Graebe : 



I. The bichlornaphtochinon fC 5 H 4 ) fC^CUOe, yields 

 on oxidation phthalic acid C. : H 4 -|cooh anc * •* is a ^ so 

 transformed by the action of pentachloride of phosphor- 

 us into the pentachloride of naphthaline (C« H 3 CI) id 

 CL) and this on oxidation produces tetrachlorphthaiic 



ariri r n i cooh. 

 acid L 6 i~i. -, cooh 



These facts prove that naphthaline is composed of 

 two symmetrical rings, and that it can only have the 

 formula of Erlenmeyer by the acceptance of Kekule's 

 benzol scheme. 



On the other hand, the ortho- (I, 2) position of phthalic 

 acid is likewise shown which was corroborated by the 

 examination of the benzol bi-derivatives (Graebe). 7 



Ladenburg' and YVreden-' have objected to Graebe's 

 method of proof, on account of the derivation of tetra- 

 chlorphthaiic acid from phtha'.ic being uncertain. It 

 can just as well be obtained from tere or isophthalthic 

 acid. This is improbable, because the tetra-chlorphthahc 

 acid used, agrees in all its properties (formation of anhy- 

 drides, etc.). with phthalic acid, and not with its two 

 isomers * 



II. Naphthalinetetrachloride (C 5 H 4 ), (d Hi Cl 4 ), 

 by oxidation gives phthalic acid C, H. | cooh (Laurent ). 

 On submitting it to dry distillation it becomes convened 

 into the a and i dichloronaphthaline (C« H 4 ) (C« H- CU; 

 and the latter (h produces, on oxidation, dichlorophtalic 

 acid C, H, CL | C q8h 'Atterbe-. 



III. Monochloronaphthalinetetrachloride C« H< (C. H t 

 CI Clu may be converted into ordinary phthalic acid by 

 oxidation. (P. and E. Depouilly " and Widman '•-.) 

 Moncchloronaphthaline, C« H. (C 4 H 3 CI) which is the 

 basis of the above compounds may be convened into 



5 Das Naphtaln und seine Denvate. Braunschweig 118701. 



I Deutsche Chem. Ges., IX. =0 



7 Ann. Chem. Pharm.. CXLIX. 1 



- Theorie der aromatischen V'erbindungen Braunschweig. 



* Deutche Chem. Ges., IX 547(1877). 



10 Deutsche Chem. Ges. IX." _- S77 



II Soc. Chim.. Paris, IV, 10. (1865V 



'■- Om Naftalins Rlorforeningar, Upsala, 1877, p. 16. Soc Chim 



- 

 *Wreden thought it might possibly have the constitution. 



CI 



c 



CI 



— c — 



C — COOH 



I 



C — COOH 



C — C 



CI — CI 



that is to say, be derived from an isometric hypo the: - 

 however, extremely improbable. 



Tki 



